(R,r)-八氢-苯并咪唑-2-硫酮 | 139237-77-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: (R,r)-八氢-苯并咪唑-2-硫酮
• 英文名称: (R,R)-(+)-trans-4,5-tetramethyleneimidazolidine-2-thione
• 英文别名: (3aR,7aR)-octahydro-2H-benzo[d]imidazole-2-thione；(3aR,7aR)-hexahydro-1H-benzo[d]imidazole-2(3H)-thione；(R,R)-Octahydro-benzoimidazole-2-thione；(3aR,7aR)-1,3,3a,4,5,6,7,7a-octahydrobenzimidazole-2-thione
• CAS: 139237-77-7
• 化学式: C₇H₁₂N₂S
• mdl: MFCD06657732
• 分子量: 156.252
• InChiKey: INYFNNKRGLROQV-PHDIDXHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.857
• 拓扑面积：
  56.2
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R,r)-八氢-苯并咪唑-2-硫酮 在 吡啶 、 4-二甲氨基吡啶 、 mercury(II) diacetate 作用下， 以 二氯甲烷 为溶剂， 生成 1,3-dipropionyl-trans-4,5-tetramethyleneimidazolin-2-one
  参考文献：
  名称：

  Bifunctional chiral auxiliaries 5: The synthesis of 1,3-diacylimidazolidine-2-thiones and 1,3-diacylimidazolidin-2-ones from 1,2-diamines

  摘要：

  Although 1,2-diamines fail to cyclise with urea, phosgene or 1,1'-carbonyl diimidazole, they react with carbon disulphide to give the corresponding imidazolidine-2-thiones. These undergo clean diacylation to give 1,3-diacylimidazolidine-2-thiones which are readily converted to 1,3-diacylimidazolidin-2-ones on treatment with mercury (II) acetate. An alternative two-step route to 1,3-diacylimidazolidin-2-ones uses carbonyl sulphide to effect cyclisation of the 1,2-diamine to the imidazolidin-2-one, which is subsequently diacylated. The ability to convert homochiral 1,2-diamines to homochiral 1,3-diacylimidazolidin-2-ones has also been demonstrated.

  DOI：

  10.1016/s0040-4020(01)85757-4
• 作为产物：
  描述：

  二硫化碳 、 (1R,2R)-1,2-diaminocyclohexane 在 盐酸 作用下， 生成 (R,r)-八氢-苯并咪唑-2-硫酮
  参考文献：
  名称：

  Bifunctional chiral auxiliaries 5: The synthesis of 1,3-diacylimidazolidine-2-thiones and 1,3-diacylimidazolidin-2-ones from 1,2-diamines

  摘要：

  Although 1,2-diamines fail to cyclise with urea, phosgene or 1,1'-carbonyl diimidazole, they react with carbon disulphide to give the corresponding imidazolidine-2-thiones. These undergo clean diacylation to give 1,3-diacylimidazolidine-2-thiones which are readily converted to 1,3-diacylimidazolidin-2-ones on treatment with mercury (II) acetate. An alternative two-step route to 1,3-diacylimidazolidin-2-ones uses carbonyl sulphide to effect cyclisation of the 1,2-diamine to the imidazolidin-2-one, which is subsequently diacylated. The ability to convert homochiral 1,2-diamines to homochiral 1,3-diacylimidazolidin-2-ones has also been demonstrated.

  DOI：

  10.1016/s0040-4020(01)85757-4
• 作为试剂：
  描述：

  3-甲基-2-丁烯醛 在 palladium on activated charcoal 3 A molecular sieve 、 氢气 、 三乙胺 、 (R,r)-八氢-苯并咪唑-2-硫酮 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 163.0h， 生成 <(1R)-1-amino>-3-methylbutyl>phosphonic acid
  参考文献：
  名称：

  Thiourea-Catalyzed Enantioselective Hydrophosphonylation of Imines:  Practical Access to Enantiomerically Enriched α-Amino Phosphonic Acids

  摘要：

  Chiral thiourea 1b catalyzes the highly enantioselective hydrophosphonylation of a wide range of N-benzyl imines. The hydrophosphonylation products are readily deprotected by hydrogenolysis, providing access to free alpha-amino phosphonic acids in highly enantioenriched form.

  DOI：

  10.1021/ja0494398

文献信息

• [EN] IMIDAZOLINE DERIVATIVES AS CXCR4 MODULATORS<br/>[FR] DÉRIVÉS D'IMIDAZOLINE UTILISÉS EN TANT QUE MODULATEURS DE CXCR4
  申请人：UNIV PARIS

  公开号：WO2020201096A1

  公开（公告）日：2020-10-08

  The present invention provides novel compounds of formula (I) and pharmaceutical compositions containing these compounds. The compounds of formula (I) can act as CXCR4 modulators that specifically target the CXCR4 minor pocket, and they have further been found to inhibit the production of inflammatory cytokines in immune cells, which renders these compounds highly advantageous for use in therapy, particularly in the treatment or prevention of an inflammatory disorder, an autoimmune disorder, an autoinflammatory disorder, or an interferonopathy, such as, e.g., lupus erythematosus, dermatomyositis or rheumatoid arthritis.

  本发明提供了化合物的新结构（I）及含有这些化合物的药物组合物。式（I）化合物可以作为CXCR4调节剂，特异性靶向CXCR4小口袋，并且进一步发现能够抑制免疫细胞中炎症细胞因子的产生，使得这些化合物在治疗中具有极大的优势，特别适用于治疗或预防炎症性疾病、自身免疫性疾病、自身炎症性疾病或干扰素病，例如红斑狼疮、皮肌炎或类风湿性关节炎。
• [EN] CYCLIC ISOTHIOUREA DERIVATIVES AS CXCR4 MODULATORS<br/>[FR] DÉRIVÉS D'ISOTHIO-URÉE CYCLIQUES UTILISÉS COMME MODULATEURS DU CXCR4
  申请人：ERMIUM THERAPEUTICS

  公开号：WO2022064075A1

  公开（公告）日：2022-03-31

  The present invention provides novel compounds of formula (I) and pharmaceutical compositions containing these compounds. The compounds of formula (I) can act as CXCR4 modulators that specifically target the CXCR4 minor pocket, and they have further been found to inhibit the production of inflammatory cytokines in immune cells, which renders these compounds highly advantageous for use in therapy, particularly in the treatment or prevention of an inflammatory disorder, an autoimmune disorder, an autoinflammatory disorder, or an interferonopathy, such as, e.g., systemic lupus erythematosus, dermatomyositis or rheumatoid arthritis.

  本发明提供了式（I）的新化合物和含有这些化合物的药物组合物。式（I）的化合物可以作为CXCR4调节剂，特异性靶向CXCR4小口袋，并且已经发现它们抑制免疫细胞中炎性细胞因子的产生，这使得这些化合物在治疗中具有极大的优势，特别是在治疗或预防炎症性疾病、自身免疫性疾病、自身炎症性疾病或干扰素病中，例如系统性红斑狼疮、皮肌炎或类风湿性关节炎。
• [EN] SELECTIVE HDAC6 INHIBITOR<br/>[FR] INHIBITEUR SÉLECTIF DE HDAC6
  申请人：ROYAL COLLEGE SURGEONS IRELAND

  公开号：WO2022129256A1

  公开（公告）日：2022-06-23

  A compound, which is according to formula (I) or is a pharmaceutically acceptable salt, solvate, ester or pro-drug thereof, for use as a medicament, wherein either (i) NR1R2together forms a 5- or 6- membered heterocyclic ring or (ii) R1and R2are independently selected from H and C1 to C12 alkyl; A is a non-aromatic ring, an aromatic ring or a double bond; X is NR3, S or O, where R3is selected from H and C1 to C12 alkyl; Y is S, NR4, CR4R5, or O, where R4and R5are independently selected from H and C1 to C12 alkyl; and Z is (CR6R7)n where R6and R7are independently selected from H and C1 to C12 alkyl and n is an integer from 1 to 6. The compounds of formula I are particularly useful for the treatment of cancer, neurodegenerative diseases and/or inflammation.

  根据公式(I)或其药学上可接受的盐、溶剂化合物、酯或前药，用作药物的化合物，其中要么(i) NR1R2共同形成5或6元杂环环，要么(ii) R1和R2分别选择自H和C1到C12烷基；A是非芳香环、芳香环或双键；X是NR3、S或O，其中R3选择自H和C1到C12烷基；Y是S、NR4、CR4R5或O，其中R4和R5独立选择自H和C1到C12烷基；Z是（CR6R7）n，其中R6和R7独立选择自H和C1到C12烷基，n是1至6的整数。公式I的化合物特别适用于治疗癌症、神经退行性疾病和/或炎症。
• POLYCYCLIC COMPOUNDS, TERMED CALIXURENES, AND USES THEREOF
  申请人：Keinan Ehud

  公开号：US20120142912A1

  公开（公告）日：2012-06-07

  Disclosed is a novel family of macrocyclic compounds, coined calixurenes, which comprises linear and cyclic oligomers composed of alternating moieties of an aromatic unit and a ureatic unit, linked to one another via a bridging moiety. The disclosed calixurenes feature multiple heteroatom-containing groups, and can be designed so as to feature other functionalities, and can thus be used in a variety of applications. Further disclosed are processes of preparing the calixurenes, articles containing same and uses thereof.
• IMIDAZOLINE DERIVATIVES AS CXCR4 MODULATORS
  申请人：Université de Paris

  公开号：US20220144853A1

  公开（公告）日：2022-05-12

  The present invention provides novel compounds of formula (I) and pharmaceutical compositions containing these compounds. The compounds of formula (I) can act as CXCR4 modulators that specifically target the CXCR4 minor pocket, and they have further been found to inhibit the production of inflammatory cytokines in immune cells, which renders these compounds highly advantageous for use in therapy, particularly in the treatment or prevention of an inflammatory disorder, an autoimmune disorder, an autoinflammatory disorder, or an interferonopathy, such as, e.g., lupus erythematosus, dermatomyositis or rheumatoid arthritis.