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CN-122029153-A - Aromatic hydrocarbon receptor modulator compound, and preparation method and application thereof

CN122029153ACN 122029153 ACN122029153 ACN 122029153ACN-122029153-A

Abstract

An aromatic hydrocarbon receptor modulator compound represented by the following formula I, and a preparation method and application thereof, wherein each optical isomer, deuterated compound, prodrug or pharmaceutically acceptable salt thereof. The compound can be used as an aromatic hydrocarbon receptor modulator for regulating the activity of an aromatic hydrocarbon receptor in vivo, and has very important significance for treating related diseases such as immunity, inflammation, infection, skin diseases, osteoporosis, cancers, neurodegenerative diseases and the like.

Inventors

  • ZHANG SUOMING

Assignees

  • 德明药泰生物技术（深圳）有限公司

Dates

Publication Date
20260512
Application Date
20241014
Priority Date
20231018

Claims (9)

  1. An aromatic hydrocarbon receptor modulator compound represented by the following formula I, each of which is an optical isomer, deuterate, prodrug or pharmaceutically acceptable salt thereof: Wherein R 1 and R 2 are each independently hydrogen, deuterium, halogen, cyano, substituted OR unsubstituted C 1-8 alkyl, substituted OR unsubstituted C 3 -C 8 cycloalkyl, substituted OR unsubstituted C 1-8 alkenyl, substituted OR unsubstituted C 1-8 alkynyl, wherein the "substituted" means containing 1-6R a substituents, wherein R a is selected from hydrogen, deuterium, halogen, OR a1 、S(O)nR a2 、NR a3 R a4 、CO 2 R a5 ; wherein R a1 and R a2 are each independently selected from hydrogen, hydroxy, amino, C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl, -C (=o) C 1-8 alkyl, -C (=o) C 3 -C 8 cycloalkyl, -C (=o) OC 1 -C 8 alkyl, -C (=o) OC 3 -C 8 cycloalkyl, -C (=o) NC 1 -C 8 alkyl, -C (=o) NC 3 -C 8 cycloalkyl; r a3 and R a4 are each independently selected from hydrogen, C 1 -C 3 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 3 alkyl substituted by halogen or hydroxy, C 3 -C 6 cycloalkyl substituted by halogen or hydroxy, C 1 -C 3 alkoxy, C 3 -C 6 cycloalkoxy, C 1 -C 3 alkoxy substituted by halogen or hydroxy, C 3 -C 6 cycloalkoxy substituted by halogen or hydroxy; R a5 is selected from hydrogen, C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl; R 3 is hydrogen, deuterium, halogen, NR b3 R b4 , substituted OR unsubstituted C 1-10 alkyl, substituted OR unsubstituted C 3 -C 12 cycloalkyl, substituted OR unsubstituted C 1-10 alkenyl, substituted OR unsubstituted C 1-10 alkynyl, C 6 -C 14 aryl, substituted OR unsubstituted 5-to 14-membered heteroaryl containing 1 to 3 heteroatoms selected from N, O and S, substituted OR unsubstituted 4-to 14-membered heterocycloalkyl containing 1 to 3 heteroatoms selected from N, O and S, wherein the "substituted" refers to containing 1-6R b substituents, wherein R b is selected from hydrogen, deuterium, halogen, OR b1 、S(O)nR b2 、NR b3 R b4 、CO 2 R b5 ; Wherein R b1 and R b2 are each independently selected from hydrogen, hydroxy, amino, C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl, -C (=o) C 1-8 alkyl, -C (=o) C 3 -C 8 cycloalkyl, -C (=o) OC 1 -C 8 alkyl, -C (=o) OC 3 -C 8 cycloalkyl, -C (=o) NC 1 -C 8 alkyl, -C (=o) NC 3 -C 8 cycloalkyl; R b3 and R b4 are each independently selected from hydrogen, C 1 -C 3 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 3 alkyl substituted by halogen or hydroxy, C 3 -C 6 cycloalkyl substituted by halogen or hydroxy, C 1 -C 3 alkoxy, C 3 -C 6 cycloalkoxy, C 1 -C 3 alkoxy substituted by halogen or hydroxy, C 3 -C 6 cycloalkoxy substituted by halogen or hydroxy; r b5 is selected from hydrogen, C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl; R 4 and R 4 ' are hydrogen, deuterium, halogen, hydroxy, C 1-8 alkyl, C 1-8 alkoxy, C 2-8 alkenyloxy, C 3 -C 10 cycloalkyl, C 3-10 cycloalkoxy, C 3-10 cycloalkenyloxy, (C 1-8 alkoxy) C 1-8 alkoxy, (C 2-8 alkenyl) C 1-8 alkoxy, (C 2-8 alkynyl) C 1-8 alkoxy, C 6 -C 14 aryl, boronate; Alternatively, R 4 or R 4 ' may form a substituted or unsubstituted C 3 -C 8 cycloalkyl ring with R 3 or a 4 to 10 membered heterocyclyl containing 1 to 3 heteroatoms selected from N, O, S and B, wherein the "substituted" means containing 1-6R a1 ; Ring a is C 6-14 aryl, a 5-14 membered heteroaryl containing from 1 to 3 heteroatoms selected from N, O and S, a substituted or unsubstituted 5-14 membered heterocycloalkyl containing from 1 to 3 heteroatoms selected from N, O and S; wherein said "substitution" means containing 1 to 6R c substituents wherein R c is selected from the group consisting of hydrogen, Deuterium, halogen, cyano, hydroxy, carbonyl, carboxyl, C 1 -C 3 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 3 alkyl substituted by halogen or hydroxy, C 3 -C 6 cycloalkyl substituted by halogen or hydroxy, C 1 -C 3 alkoxy, C 3 -C 6 cycloalkoxy, C 1 -C 3 alkoxy substituted by halogen or hydroxy, C 3 -C 6 cycloalkoxy substituted by halogen or hydroxy, NR c1 R c2 、CO 2 R c3 wherein R c1 and R c2 are each independently selected from the group consisting of hydrogen, C 1 -C 3 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 3 alkyl substituted by halogen or hydroxy, C 3 -C 6 cycloalkyl substituted by halogen or hydroxy, C 1 -C 3 alkoxy, C 3 -C 6 cycloalkoxy, C 1 -C 3 alkoxy substituted by halogen or hydroxy, C 3 -C 6 cycloalkoxy substituted by halogen or hydroxy, R c3 is selected from hydrogen, C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl; R 5 is selected from hydrogen, deuterium, halogen, cyano, hydroxy, carbonyl, carboxyl, C 1 -C 3 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 3 alkoxy, C 3 -C 6 Cycloalkoxy, C 1 -C 3 alkyl substituted by halogen or hydroxy, C 3 -C 6 cycloalkyl substituted by halogen or hydroxy, C 1 -C 3 alkoxy substituted by halogen or hydroxy, C 3 -C 6 Cycloalkoxy substituted with halogen or hydroxy, NR d1 R d2 、CO 2 R d3 wherein R d1 and R d2 are each independently selected from hydrogen, C 1 -C 3 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 3 alkyl substituted by halogen or hydroxy, C 3 -C 6 cycloalkyl substituted by halogen or hydroxy, C 1 -C 3 alkoxy, C 3 -C 6 cycloalkoxy, C 1 -C 3 alkoxy substituted by halogen or hydroxy, C 3 -C 6 cycloalkoxy substituted by halogen or hydroxy, R d3 is selected from hydrogen, C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl; But does not include the following:
  2. The aromatic hydrocarbon receptor modulator compound represented by the formula I according to claim 1, wherein each of the optical isomers, deuterates, prodrugs or pharmaceutically acceptable salts thereof, Preferably, R 1 and R 2 are each independently hydrogen, deuterium, halogen, cyano, substituted OR unsubstituted C 1-6 alkyl, substituted OR unsubstituted C 3 -C 6 cycloalkyl, substituted OR unsubstituted C 1-6 alkenyl, substituted OR unsubstituted C 1-6 alkynyl, wherein the "substituted" means containing 1-4R a substituents, wherein R a is selected from hydrogen, deuterium, halogen, OR a1 、S(O)nR a2 、NR a3 R a4 、CO 2 R a5 ; wherein R a1 and R a2 are each independently selected from hydrogen, hydroxy, amino, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, -C (=o) C 1-6 alkyl, -C (=o) C 3 -C 6 cycloalkyl, -C (=o) OC 1 -C 6 alkyl, -C (=o) OC 3 -C 6 cycloalkyl, -C (=o) NC 1 -C 6 alkyl, -C (=o) NC 3 -C 6 cycloalkyl; r a3 and R a4 are each independently selected from hydrogen, C 1 -C 3 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 3 alkyl substituted by halogen or hydroxy, C 3 -C 6 cycloalkyl substituted by halogen or hydroxy, C 1 -C 3 alkoxy, C 3 -C 6 cycloalkoxy, C 1 -C 3 alkoxy substituted by halogen or hydroxy, C 3 -C 6 cycloalkoxy substituted by halogen or hydroxy; R a5 is selected from hydrogen, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl; More preferably, R 1 and R 2 are each independently hydrogen, deuterium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl; preferably, R 3 is hydrogen, deuterium, halogen, NR b3 R b4 , substituted OR unsubstituted C 1-8 alkyl, substituted OR unsubstituted C 3 -C 10 cycloalkyl, substituted OR unsubstituted C 1-8 alkenyl, substituted OR unsubstituted C 1-8 alkynyl, C 6 -C 10 aryl, substituted OR unsubstituted 5-to 10-membered heteroaryl containing 1 to 3 heteroatoms selected from N, O and S, substituted OR unsubstituted 4-to 10-membered heterocycloalkyl containing 1 to 3 heteroatoms selected from N, O and S, wherein the "substituted" refers to containing 1-4R b substituents, wherein R b is selected from hydrogen, deuterium, halogen, OR b1 、S(O)nR b2 、NR b3 R b4 、CO 2 R b5 ; wherein R b1 and R b2 are each independently selected from hydrogen, hydroxy, amino, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, -C (=o) C 1-6 alkyl, -C (=o) C 3 -C 6 cycloalkyl, -C (=o) OC 1 -C 6 alkyl, -C (=o) OC 3 -C 6 cycloalkyl, -C (=o) NC 1 -C 6 alkyl, -C (=o) NC 3 -C 6 cycloalkyl; R b3 and R b4 are each independently selected from hydrogen, C 1 -C 3 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 3 alkyl substituted by halogen or hydroxy, C 3 -C 6 cycloalkyl substituted by halogen or hydroxy, C 1 -C 3 alkoxy, C 3 -C 6 cycloalkoxy, C 1 -C 3 alkoxy substituted by halogen or hydroxy, C 3 -C 6 cycloalkoxy substituted by halogen or hydroxy; R b5 is selected from hydrogen, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl; More preferably, R 3 is hydrogen, deuterium, halogen, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, dimethylcyclohexyl, ethenyl, propenyl, butenyl, 3-methyl-2-butenyl; Preferably, R 4 and R 4 ' are hydrogen, deuterium, halogen, hydroxy, C 1-6 alkyl, C 1-6 alkoxy, C 2-6 alkenyloxy, C 3-6 cycloalkyl, C 3-6 cycloalkoxy, C 3-6 cycloalkenyloxy, (C 1-6 alkoxy) C 1-6 alkoxy, (C 2-6 alkenyl) C 1-6 alkoxy, (C 2-6 alkynyl) C 1-6 alkoxy, C 6 -C 14 aryl, boronate; More preferably, R 4 and R 4 ' are hydrogen, deuterium, halogen, hydroxy, C 1- C 6 alkyl, C 3 -C 6 cycloalkyl, C 6 -C 10 aryl, boronic acid, boronic ester; Preferably, R 4 and R 4 ' are hydrogen, deuterium, halogen, hydroxy, methyl, ethyl, n-propyl, isopropyl, boric acid ester; Preferably, R 4 and R 4 ' are hydrogen or deuterium Preferably, R 4 or R 4 ' may form a substituted or unsubstituted C 3 -C 6 cycloalkyl group with R 3 ring formation or a 4 to 8 membered heterocyclyl group containing 1 to 3 heteroatoms selected from N, O, S and B, wherein the "substituted" means containing 1-4R a1 ; Preferably, R 4 or R 4 ' may form a substituted or unsubstituted C 3 -C 6 cycloalkyl group with R 3 ring formation or a 4 to 6 membered heterocyclyl group containing 1 to 2 heteroatoms selected from N, O, S and B, wherein the "substituted" means containing 1-3R a1 ; Preferably, the A ring is a C 6-10 aryl group, a 5-10 membered heteroaryl group containing 1 or 2 heteroatoms selected from N, O and S, a substituted or unsubstituted 5-10 membered heterocycloalkyl group containing 1 or 2 heteroatoms selected from N, O and S, wherein said "substituted" means containing 1-4R c substituents, wherein R c is selected from hydrogen, Deuterium, halogen, cyano, hydroxy, carbonyl, carboxyl, C 1 ～C 3 alkyl, C 3 ～C 6 cycloalkyl, C 1 ～C 3 alkyl substituted by halogen or hydroxy, C 3 ～C 6 cycloalkyl substituted by halogen or hydroxy, C 1 ～C 3 alkoxy, C 3 ～C 6 cycloalkoxy, C 1 ～C 3 alkoxy substituted by halogen or hydroxy, C 3 ～C 6 cycloalkoxy substituted by halogen or hydroxy, NR c1 R c2 、CO 2 R c3 wherein R c1 and R c2 are each independently selected from the group consisting of hydrogen, C 1 ～C 3 alkyl, C 3 ～C 6 cycloalkyl, C 1 ～C 3 alkyl substituted by halogen or hydroxy, C 3 ～C 6 cycloalkyl substituted by halogen or hydroxy, C 1 ～C 3 alkoxy, C 3 ～C 6 cycloalkoxy, C 1 ～C 3 alkoxy substituted by halogen or hydroxy, C 3 ～C 6 cycloalkoxy substituted by halogen or hydroxy, R c3 is selected from hydrogen, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl; More preferably, the a ring is: preferably, R 5 is selected from hydrogen, deuterium, halogen, cyano, hydroxy, carbonyl, carboxyl, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methoxy, ethoxy, n-propoxy, isopropoxy, cyclopropoxy, cyclobutoxy, cyclopentyloxy, cyclohexyloxy, -C (=o) O methyl, -C (=o) O ethyl, -C (=o) O n-propyl, -C (=o) O isopropyl.
  3. The aromatic hydrocarbon receptor modulator compound represented by the formula I according to claim 1, wherein each of the optical isomers, deuterates, prodrugs or pharmaceutically acceptable salts thereof, Preferably, the compound of formula I is represented by formula IIa, formula IIb or formula IIc, Wherein R 1 to R 4 ,R 4 ' are as defined in formula I in claim 1; Each of a 1 and a 4 is independently selected from C, N, O and S atoms, each of a 2 and a 3 is independently selected from C or N atoms, provided that at most two of a 1 to a 4 are simultaneously heteroatoms selected from N, O and S, and the other two are C atoms; Dotted line The indicated position may be a double bond; R 6 、R 7 and R 8 are each independently selected from hydrogen, halogen, hydroxy, carboxy, carbonyl, cyano, C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, C 1 -C 6 alkyl substituted by halogen or hydroxy, C 3 -C 8 cycloalkyl substituted by halogen or hydroxy, C 1 -C 6 alkoxy, C 3 -C 8 cycloalkoxy, C 1 -C 6 alkoxy substituted by halogen or hydroxy, C 3 -C 8 cycloalkoxy substituted by halogen or hydroxy; One or more R 6 may form with A 4 a C 3 -C 6 cycloalkyl, A3-7 membered heterocyclyl containing 1 to 3 heteroatoms selected from N, O and S, one or more R 7 may form with A 3 a C 3 -C 6 cycloalkyl, A3-7 membered heterocyclyl containing 1 to 3 heteroatoms selected from N, O and S, R d is selected from hydrogen, halogen, hydroxy, carboxy, cyano, C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, C 1 -C 6 alkyl substituted by halogen, C 1 -C 6 alkoxy, C 3 -C 8 cycloalkoxy; n1 and n2 are each independently integers of 0, 1 or 2; n3 is an integer of 0, 1,2, 3 or 4; Preferably, R 6 、R 7 and R 8 are each independently selected from hydrogen, halogen, hydroxy, carboxy, carbonyl, cyano, C 1 -C 3 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 3 alkyl substituted by halogen or hydroxy, C 3 -C 6 cycloalkyl substituted by halogen or hydroxy, C 1 -C 3 alkoxy, C 3 -C 6 cycloalkoxy, C 1 -C 3 alkoxy substituted by halogen or hydroxy, C 3 -C 6 cycloalkoxy substituted by halogen or hydroxy; more preferably, R 6 、R 7 and R 8 are each independently selected from hydrogen, halogen, hydroxy, carboxy, carbonyl, cyano, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methoxy, ethoxy, n-propoxy, isopropoxy, cyclopropoxy, cyclobutoxy, cyclopentoxy, cyclohexyloxy; Preferably, one or more R 6 may form with a 4 a C 3 -C 6 cycloalkyl, A3-6 membered heterocyclyl containing 1 to 2 heteroatoms selected from N, O and S, and one or more R 7 may form with a 3 a C 3 -C 6 cycloalkyl, A3-6 membered heterocyclyl containing 1 to 2 heteroatoms selected from N, O and S; Preferably, R d is selected from hydrogen, halogen, hydroxy, carboxy, cyano, C 1 -C 3 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 3 alkyl substituted by halogen, C 1 -C 3 alkoxy, C 3 -C 6 cycloalkoxy; More preferably, R d is selected from hydrogen, halogen, hydroxy, carboxy, cyano, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methoxy, ethoxy, n-propoxy, isopropoxy, cyclopropoxy, cyclobutoxy, cyclopentoxy, cyclohexyloxy; preferably, n1 and n2 are each independently integers of 0,1 or 2; preferably, n3 is an integer of 0, 1 or 2.
  4. The aromatic hydrocarbon receptor modulator compound represented by the formula I according to claim 1, wherein each of the optical isomers, deuterates, prodrugs or pharmaceutically acceptable salts thereof, Preferably, the compound represented by formula I is represented by formula IIIa or formula IIIb below, Wherein R 1 to R 4 ,R 4 ' are as defined in formula I in claim 1; Each of a 1 to a 6 is independently selected from C, N, O and S atoms, a 2 is a C or N atom, provided that at most two of a 1 to a 6 are simultaneously heteroatoms selected from N, O and S, the remainder being C atoms; Dotted line The indicated position may be a double bond; Each R 9 is independently selected from hydrogen, halogen, hydroxy, carboxy, carbonyl, cyano, C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl, C 6 -C 14 aryl, C 6 -C 14 aryl substituted with halogen, -C (=o) OC 1 -C 8 alkyl, 5-10 membered heteroaryl containing hetero 1 or 2 heteroatoms selected from N, O and S, 5-10 membered heterocycloalkyl containing 1 or 2 heteroatoms selected from N, O and S; n4 is an integer of 0, 1,2, 3 or 4; Preferably, R 8 and R 9 are each independently selected from hydrogen, halogen, hydroxy, carboxy, carbonyl, cyano, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 6 -C 10 aryl, C 6 -C 10 aryl substituted by halogen, -C (=o) OC 1 -C 6 alkyl, 5-to 6-membered heteroaryl containing 1 or 2 heteroatoms selected from N, O and S, 5-to 6-membered heterocycloalkyl containing 1 or 2 heteroatoms selected from N, O and S; Preferably, each R 9 is independently selected from hydrogen, halogen, hydroxy, carboxy, carbonyl, cyano, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methyl ester, ethyl ester, n-propyl ester, isopropyl ester, furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl; preferably, n4 is an integer of 0, 1 or 2.
  5. The aromatic hydrocarbon receptor modulator compound represented by formula I according to claim 1, wherein the compound represented by formula I is selected from the group consisting of optical isomers, deuterates, prodrugs and pharmaceutically acceptable salts thereof:
  6. A pharmaceutical composition comprising a therapeutically effective amount of an aromatic hydrocarbon receptor modulator compound represented by formula I, formula IIa, formula IIb, formula IIc, formula IIIa or formula IIIb according to any one of claims 1 to 5, each of which is an optical isomer, deuterate, prodrug or pharmaceutically acceptable salt thereof and a pharmaceutically acceptable excipient or carrier.
  7. An aromatic hydrocarbon receptor modulator compound represented by formula I, formula IIa, formula IIb, formula IIc, formula IIIa or formula IIIb as defined in any one of claims 1 to 5, and a compound The use of their respective optical isomers, deuterates, prodrugs or pharmaceutically acceptable salts as AHR pathway modulators.
  8. An aromatic hydrocarbon receptor modulator compound represented by formula I, formula IIa, formula IIb, formula IIc, formula IIIa or formula IIIb as defined in any one of claims 1 to 5, and a compound Use of the respective optical isomer, deuterate, prodrug or pharmaceutically acceptable salt thereof for the preparation of a medicament for the treatment of a tumor associated with the AHR pathway.
  9. A method of treating a tumor associated with the AHR pathway, the method comprising administering to a subject in need thereof an effective amount of an aromatic receptor modulator compound represented by formula I, formula IIa, formula IIb, formula IIc, formula IIIa, or formula IIIb according to any one of claims 1 to 5, and a compound Each of which is an optical isomer, a deuterate, a prodrug or a pharmaceutically acceptable salt thereof or the pharmaceutical composition according to the invention.

Description

Aromatic hydrocarbon receptor modulator compound, and preparation method and application thereof The present application claims the priority benefit of chinese patent application, filed 10/18/2023, entitled "aromatic receptor modulators compounds and methods for their preparation and use", to the chinese intellectual property office of China, application No. 202311351389.X, the entire contents of which are hereby incorporated by reference. Technical Field The invention belongs to the technical field of biological pharmacy, and particularly relates to an aromatic hydrocarbon receptor modulator compound, its respective optical isomer, deuterated substance, prodrug or pharmaceutically acceptable salt, and a preparation method and application thereof. Background Aromatic hydrocarbon receptors (AHR, aryl Hydrocarbon Receptor) are one of the subfamily bHLH-PAS (bHLH-PER-ARNT-SIM) members of the basic helix-loop-helix (bHLH, basic helix-loop-helix) superfamily, are the only receptors in the bHLH-PAS family that can be activated by ligands [ Murray et al, nat. Rev. Cancer,2014,14 (12), 801-814; berstenet al, nat. Rev. Cancer,2013,13 (12), 827-841]. AHR present in the cytoplasm is capable of receiving stimulation of an aromatic hydrocarbon heteroconjugate (xenobiotic), such as 2,3,7, 8-tetrachlorodibenzo-dioxin (TCDD, tetrachlorodibenzo-p-dioxan), and then migrate into the nucleus to form a heterodimer with an aromatic hydrocarbon receptor nuclear transporter (ARNT, aryl Hydrocarbon Receptor Nuclear Translocator), and the AHR/ARNT complex then interacts with a foreign genetic response element (XRE, xenobiotic response element) upstream of the AHR regulatory gene to regulate transcription of the corresponding gene, and AHR also activates a non-XRE dependent protein-protein interaction pathway. The AHR pathway is one of the most well known to bind environmental toxins and induce metabolic mechanisms, such as regulated cytochrome CYP450 enzymes (e.g., CYP1A1, CYP1A2 and CYP1B 1), which metabolize environmental toxins [ (Reyes et al, science,1992,256 (5060), 1193-1195;Murray et al ], nat. Rev. Cancer,2014,14 (12), 801-814]. Activation of AHR by environmental toxins has been shown to play a role in numerous cellular processes, such as embryogenesis, tumorigenesis and inflammation AHR is expressed in many cells of the immune system, including dendritic cells, macrophages, T-cells and NK cells, and plays an important role in immunomodulation (Nguyen et al., front. Immunol 2014,5,511). Classical exogenous AHR ligand TCDD, etc. induces deep immunosuppression, promotes carcinogenesis and induces tumor growth [Gramatzkietal.,Oncogene,2009,28(28),2593-2605;Buietal.,Oncogene,2009,28(41),3642-3651;Esseretal.,Trends.Immunol.,2009,30(9),447-454]. AHR regulates many key innate and adaptive immune responses through XRE-dependent or independent activities. Some AHR agonists were found to promote differentiation of Th 17-producing cells (T-HELPER CELLS) and secretion of IL-17. While other AHR agonists may induce lateral differentiation of Th17 cells into Treg cells, potentiating the inhibitory activity of Treg [ Quintana et al., nature,2008,453 (7191), 65-71; mezrich et al, J.Immunol.,2010,185 (6), 3190-3198 ]. Studies have shown that AHR activation can inhibit macrophage-mediated innate inflammatory response (e.g., reduce Lipopolysaccharide (LPS) -induced IL-1b, IL-6, IL-12 and TNF-alpha expression), and dendritic cell inhibition (reduce dendritic cell activation and promote IL-10 expression) )[Kimura et al.,J.Exp.Med.,2009,206(9),2027-2035;Wang et al.,Clin.Exp.Immunol.,2014,177(2),521-530;Weiet al.,Lab.Invest.,2014,94(5),528-535;Nguyen et al.,Proc.Natl.Acad.Sci.USA,2010,107(46),19961-19966]. Whether a compound is an aromatic hydrocarbon receptor modulator can be determined by a method of detecting whether the compound upregulates downstream related genes (CYP 1A1, CYP1B1, etc.) and related protein expression levels (CYP 1A1, CYP1B1, etc.) through a signaling pathway. By regulating the signal pathway of the aromatic hydrocarbon receptor, the activity of the related exogenous substance metabolizing enzyme of the downstream target genes (such as CYP1A1, CYP1A2 and CYP1B 1) can be regulated, and the regulation of the activity of the aromatic hydrocarbon receptor has an important influence on the composition and activity of immune cells in the body. Therefore, the aromatic hydrocarbon receptor activity is regulated, and the method has very important significance for treating related diseases such as immunity, inflammation, infection, skin diseases, osteoporosis, cancers, neurodegenerative diseases and the like. Disclosure of Invention Thus, according to a first aspect of the present invention, it is an object of the present invention to provide a class of aromatic hydrocarbon receptor modulator compounds represented by the following formula I, each of which is an optical isomer, deuterate, prodrug or pharmaceutically acceptable salt there