反式-2-羟甲基-1-环己胺 盐酸盐 | 28250-45-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 反式-2-羟甲基-1-环己胺 盐酸盐
• 中文别名: 反式-2-羟甲基-1-环己胺盐酸盐
• 英文名称: (+/-)-trans-2-hydroxymethyl-1-cyclohexylamine hydrochloride
• 英文别名: (+/-)-(trans-2-amino-cyclohexyl)-methanol; hydrochloride；Trans-2-hydroxymethyl-1-cyclohexylamine hydrochloride；[(1R,2R)-2-aminocyclohexyl]methanol;hydrochloride
• CAS: 28250-45-5
• 化学式: C₇H₁₅NO*ClH
• mdl: MFCD00145424
• 分子量: 165.663
• InChiKey: ORPKUPNVXFLMRG-UOERWJHTSA-N

物化性质

• 熔点：
  150-155 °C

计算性质

• 辛醇/水分配系数(LogP)：
  0.14
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  3
• 氢受体数：
  2

安全信息

• 安全说明：
  S24/25

反应信息

• 作为反应物：
  描述：

  反式-2-羟甲基-1-环己胺 盐酸盐 在 palladium on activated charcoal 草酰氯 、 氢气 、 三乙酰氧基硼氢化钠 、 sodium carbonate 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、344.74 kPa 条件下， 生成 (1R,2S)-2-[[4-[(4-fluorophenyl)methyl]piperidin-1-yl]methyl]cyclohexan-1-amine
  参考文献：
  名称：

  Discovery of CC Chemokine Receptor-3 (CCR3) Antagonists with Picomolar Potency

  摘要：

  Starting with our previously described(20) class of CC chemokine receptor-3 (CCR3) antagonist, we improved the potency by replacing the phenyl linker of 1 with a cyclohexyl linker and by replacing the 4-benzylpiperidine with a 3-benzylpiperidine. The resulting compound, 32, is a potent and selective antagonist of CCR3. SAR studies showed that the 3-acetylphenyl urea of 32 could be replaced with heterocyclic ureas or heterocyclic-substituted phenyl ureas and still maintain the potency (inhibition of eotaxin-induced chemotaxis) of this class of compounds in the low-picomolar range (IC50 = 10-60 pM), representing some of the most potent CCR3 antagonists reported to date. The potency of 32 for mouse CCR3 (chemotaxis IC50 = 41 nM) and its oral bioavailability in mice (20% F) were adequate to assess the efficacy in animal models of allergic airway inflammation. Oral administration of 32 reduced eosinophil recruitment into the lungs in a dose-dependent manner in these animal models. On the basis of its overall potency, selectivity, efficacy, and safety profile, the benzenesulfonate salt of 32, designated DPC168, entered phase 1 clinical trials.

  DOI：

  10.1021/jm049530m

文献信息

• [EN] SULPHONYLAMINO DERIVATIVES FOR THE TREATMENT OF ALZHEIMER'S DISEASE<br/>[FR] DERIVES SULFONYLAMINO POUR LE TRAITEMENT DE LA MALADIE D'ALZHEIMER
  申请人：NOVO PHARMACEUTICALS LTD DE

  公开号：WO2004020402A1

  公开（公告）日：2004-03-11

  A compound of formula (I), wherein R1 is alkyl, alkenyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, heterocycloalkenyl, aryl, heteroaryl, heteropolycyclyl or polycyclyl, any of which is optionally substituted with alkyl, heteroaryl, aryl or -O-aryl; R2 is alkyl, alkenyl or aryl, any of which is optionally substituted with hydroxy, halogen, aryl, heteroaryl, cycloalkyl, cycloalkenyl, -C(O)NH-aryl, heterocycloalkyl, heterocycloalkenyl, heteropolycyclyl or polycyclyl; R3 is hydrogen or aryl; R4 is alkyl, alkenyl, alkoxy, alkylthio or aryl, any of which is optionally substituted with hydroxy, aryl, heteroaryl, cycloalkyl, cycloalkenyl, thioalkyl, heterocycloalkyl, heterocycloalkenyl, heteropolycyclyl or polycyclyl; R5 is hydrogen or an alkyl or alkenyl group optionally substituted with hydroxy, aryl, -C(O)O- alkyl or -C(O)NH- alkyl; or R4-C-R5 taken together form cycloalkyl, cycloalkenyl or polycyclyl, any of which is optionally substituted with alkyl or hydroxyalkyl; R6 is hydrogen, alkyl, -alkyl-aryl or -alkyl-heteroaryl; or a pharmaceutically-acceptable salt thereof.

  公式(I)的化合物，其中R1是烷基、烯基、环烷基、环烯基、杂环烷基、杂环烯基、芳基、杂芳基、杂多环烷基或多环烷基，任选地被烷基、杂芳基、芳基或-O-芳基取代；R2是烷基、烯基或芳基，任选地被羟基、卤素、芳基、杂芳基、环烷基、环烯基、-C(O)NH-芳基、杂环烷基、杂环烯基、杂多环烷基或多环烷基取代；R3是氢或芳基；R4是烷基、烯基、烷氧基、硫代烷基或芳基，任选地被羟基、芳基、杂芳基、环烷基、环烯基、硫代烷基、杂环烷基、杂环烯基、杂多环烷基或多环烷基取代；R5是氢或烷基或烯基，任选地被羟基、芳基、-C(O)O-烷基或-C(O)NH-烷基取代；或者R4-C-R5共同形成环烷基、环烯基或多环烷基，任选地被烷基或羟基烷基取代；R6是氢、烷基、-烷基-芳基或-烷基-杂芳基；或其药物可接受的盐。
• [EN] CHEMICAL COMPOUNDS<br/>[FR] DERIVES DE QUINAZOLINE POUR LE TRAITEMENT DU CANCER
  申请人：ASTRAZENECA AB

  公开号：WO2004094410A1

  公开（公告）日：2004-11-04

  Quinazoline derivatives of formula (I); for use in the treatment of proliferative diseases such as cancer and in the preparation of medicaments for use in the treatment of proliferative diseases, and to processes for their preparation, as well as pharmaceutical compositions containing them as active ingredient.

  公式（I）的喹唑啉衍生物；用于治疗癌症等增殖性疾病，并用于制备用于治疗增殖性疾病的药物，以及它们的制备方法，以及含有它们作为活性成分的药物组合物。
• Synthesis and Conformational Analysis of Saturated3,1,2-Benzoxazaphosphinine 2-Oxides
  作者：Henri Kivelä、Zita Zalán、Petri Tähtinen、Reijo Sillanpää、Ferenc Fülöp、Kalevi Pihlaja

  DOI：10.1002/ejoc.200400611

  日期：2005.3

  synthesize P-epimeric diastereomers of the corresponding unsubsituted and N-substituted 2-phenyl-, 2phenoxy- and 2-[bis(2-chloroethyl)amino]octahydro-2H3,1,2-benzoxazaphosphinine 2-oxides. The stereochemistry and conformations of the prepared compounds were analyzed mainly by variable-temperature 1 H, 13 C and 31 P NMR spectroscopy. Geometry optimizations were performed for some trans-fused molecules

  N-未取代的 N-甲基和 N-苄基顺式和反式 2（羟甲基）环己胺与二氯苯膦、二氯磷酸苯和二（2-氯乙基）二氯磷酰胺进行闭环，以合成 P-差向异构非对映异构体相应的未取代和N-取代的2-苯基-、2-苯氧基-和2-[双(2-氯乙基)氨基]八氢-2H3,1,2-苯并恶氮膦2-氧化物。制备的化合物的立体化学和构象主要通过变温 1 H、 13 C 和 31 P NMR 光谱分析。通过利用 B3LYP DFT 方法和局部密集基组，对一些转融合分子进行几何优化，然后是 JH,P coup
• NOVEL HSP90 INHIBITORY CARBAZOLE DERIVATIVES, COMPOSITIONS CONTAINING SAME AND USE THEREOF
  申请人：RUXER Jean-Marie

  公开号：US20110166169A1

  公开（公告）日：2011-07-07

  The invention relates to the novel substances in Formula (I): wherein Het is a heterocycle optionally substituted by one or a plurality of radicals R1 or R′1; R is selected from the group comprising Formula (A′), (B), (C), (D), or (E), with R1 and/or R′1 selected from H, halogen, CF3, nitro, cyano, alkyl, hydroxyl, mercapto, amino, alkylamino, dialkylamino, alkoxy, phenylalcoxy, alkylhio, or carboxy that is free or esterified by an alkyl, carboxamide, CO—NH(alkyl), CON(alkyl)2, NH—CO-alkyl, sulfonamide, NH—S02-alkyl, S(0)2-NHalkyl, or S(02)-N(alkyl)2 radical; all these radicals are optionally substituted; W1, W2, and W3 independently are CH or N; X is 0, S, NR2, C(O), S(O), or S(0)2; Z is optionally substituted H, Hal, -0-R2 or —NH—R2 with R2 being H, alkyl, cycloalkyl, or heterocycloalkyl; and these substances are all isomeric forms and salts thereof, used as drugs.

  该发明涉及式（I）中的新物质：其中Het是一种杂环，可选择地由一个或多个基团R1或R′1取代；R从包括式（A′）、（B）、（C）、（D）或（E）的基团中选择，其中R1和/或R′1从H、卤素、CF3、硝基、氰基、烷基、羟基、巯基、氨基、烷基氨基、二烷基氨基、烷氧基、苯基氧基、烷硫基或自由或被烷基、羧酰胺、CO—NH（烷基）、CON（烷基）2、NH—CO-烷基、磺酰胺、NH—S02-烷基、S(0)2-NH烷基或S(02)-N(烷基)2基团中选择；所有这些基团可选择地被取代；W1、W2和W3独立地是CH或N；X是0、S、NR2、C(O)、S(O)或S(0)2；Z是可选择地取代的H、卤素、-0-R2或—NH—R2，其中R2是H、烷基、环烷基或杂环烷基；这些物质都是同分异构体和其盐，用作药物。
• [EN] TRIAZOLOPYRIDINE COMPOUNDS AND THEIR USE AS ASK INHIBITORS<br/>[FR] COMPOSÉS DE TRIAZOLOPYRIDINE ET LEUR UTILISATION COMME INHIBITEURS DE ASK
  申请人：SERONO LAB

  公开号：WO2009027283A1

  公开（公告）日：2009-03-05

  The present invention relates to triazolopyridine compounds according to Formula (I), their use as medicament, for treating autoimmune disorders, inflammatorydiseases, cardiovascular disceases and/or neurodegenerative diseases and a process for their preparation.

  本发明涉及三唑吡啶化合物，其化学式为（I），其用作药物，用于治疗自身免疫性疾病、炎症性疾病、心血管疾病和/或神经退行性疾病，以及其制备方法。