5-氯-1H-吲唑-3-甲酸甲酯 | 1079-46-5

• 物质功能分类: 医药中间体 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 中文名称: 5-氯-1H-吲唑-3-甲酸甲酯
• 英文名称: methyl 5-chloro-1H-indazole-3-carboxylate
• 英文别名: methyl 5-chloroindazole-3-carboxylate
• CAS: 1079-46-5
• 化学式: C₉H₇ClN₂O₂
• 分子量: 210.62
• InChiKey: OFHGAYNAKIWVOL-UHFFFAOYSA-N

物化性质

• 熔点：
  207 °C
• 沸点：
  378.7±22.0 °C(Predicted)
• 密度：
  1.453±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  5-氯-1H-吲唑-3-甲酸甲酯 在 potassium hydroxide 、 sodium hydroxide 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 18.0h， 生成 5-chloro-1-methyl-1H-indazole-3-carboxylic acid
  参考文献：
  名称：

  Discovery and Pharmacological Profile of New 1H-Indazole-3-carboxamide and 2H-Pyrrolo[3,4-c]quinoline Derivatives as Selective Serotonin 4 Receptor Ligands

  摘要：

  Since the discovery of the serotonin 4 receptor (5-HT4R), a large number of receptor ligands have been studied. The safety concerns and the lack of market success of these ligands have mainly been attributed to their lack of selectivity. In this study we describe the discovery of N-[(4- piperidinyl)methyl]-1H-indazole-3-carboxamide and 4-[(4-piperidinyl)methoxy]-2H-pyrrolo[3,4-c]quinoline derivatives as new 5-HT4R ligands endowed with high selectivity over the serotonin 2A receptor and human ether-a-go-go-related gene potassium ion channel. Within these series, two molecules (11ab and 12g) were identified as potent and selective 5-HT4R antagonists with good in vitro pharmacokinetic properties. These compounds were evaluated for their antinociceptive action in two analgesia animal models. 12g showed a significant antinociceptive effect in both models and is proposed as an interesting lead compound as a 5-HT4R antagonist with analgesic action.

  DOI：

  10.1021/jm300573d
• 作为产物：
  描述：

  5-氯靛红 在 氯化亚砜 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 33.17h， 生成 5-氯-1H-吲唑-3-甲酸甲酯
  参考文献：
  名称：

  Scaffold hopping from indoles to indazoles yields dual MCL-1/BCL-2 inhibitors from MCL-1 selective leads

  摘要：

  选择性抑制抗凋亡BCL-2家族蛋白的抗肿瘤功效常常受到同类蛋白上调的影响。在这里，我们描述了我们开发双重MCL-1/BCL-2抑制剂的努力。

  DOI：

  10.1039/d2md00095d

文献信息

• [EN] THERAPEUTIC INHIBITORY COMPOUNDS<br/>[FR] COMPOSÉS INHIBITEURS THÉRAPEUTIQUES
  申请人：LIFESCI PHARMACEUTICALS INC

  公开号：WO2015103317A1

  公开（公告）日：2015-07-09

  The invention provides compounds of Formula I and Formula II: A-B-C-D-E-F-G-J (I) C-D-E-F-G-J (II) wherein A, B, C, D, E, F, G, and J have any of the values defined in the specification, and salts thereof. The compounds are useful for inhibiting plasma kallikrein, and for treating a disease or condition in an animal where inhibition of plasma kallikrein is indicated.

  该发明提供了Formula I和Formula II的化合物：A-B-C-D-E-F-G-J (I)和C-D-E-F-G-J (II)，其中A、B、C、D、E、F、G和J具有规范中定义的任何值，以及它们的盐。这些化合物对抑制血浆激肽酶和治疗动物中需要抑制血浆激肽酶的疾病或症状是有用的。
• CARBOXYLIC ACID, ACYL SULFONAMIDE AND ACYL SULFAMIDE-DERIVATIZED BICYCLIC AZA-HETEROAROMATICS AS SELECTIVE MCL-1 INHIBITORS AND AS DUAL MCL-1/BCL-2 INHIBITORS
  申请人：University of Maryland, Baltimore

  公开号：US20200299285A1

  公开（公告）日：2020-09-24

  Mcl-1 selective inhibitors, Bcl-2 selective inhibitors, and Mcl-1/Bcl-2 dual inhibitors and methods of using the same for the treatment of disease are disclosed.

  揭示了Mcl-1选择性抑制剂、Bcl-2选择性抑制剂以及Mcl-1/Bcl-2双重抑制剂，以及利用它们用于治疗疾病的方法。
• N-Heterocyclic Carbenes of 5-Haloindazoles Generated by Decarboxylation of 5-Haloindazolium-3-carboxylates
  作者：Andreas Schmidt、Bohdan Snovydovych、Tobias Habeck、Petra Dröttboom、Mimoza Gjikaj、Arnold Adam

  DOI：10.1002/ejoc.200700192

  日期：2007.10

  pseudo-cross-conjugated heterocyclic mesomeric betaines are described, and results of an X-ray single crystal analysis of the nonhalogenated parent compound are presented. These betaines decarboxylate on heating to yield 5-halo-1,2-dimethyl-indazol-3-ylidenes, which can be trapped by protons, sulfur, and 2,4-dichlorophenylisocyanate, respectively. The decarboxylation is studied by electrospray-ionization mass

  描述了作为拟交叉共轭杂环内消旋甜菜碱的新代表的 5-氟-、氯-溴-和碘-取代的 1,2-二甲基吲唑鎓-3-羧酸酯的合成和性质，以及 X 射线的结果提供了非卤化母体化合物的单晶分析。这些甜菜碱在加热时脱羧生成 5-halo-1,2-二甲基-吲唑-3-ylidenes，它们可以分别被质子、硫和 2,4-二氯苯基异氰酸酯捕获。通过电喷雾电离质谱、核磁共振光谱、热重分析和差示扫描量热法研究脱羧。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Quantum mechanical study and vibrational spectra of indazolium-3-carboxylate and its decarboxylation product, the N-heterocyclic carbene indazol-3-ylidene
  作者：Andreas Schmidt、Bohdan Snovydovych、Juan Casado、José Joaquín Quirante、Juan Teodomiro López Navarrete、Francisco Javier Ramírez

  DOI：10.1039/b812597j

  日期：——

  nucleus of several pseudo-cross-conjugated mesomeric betaines, such as the alkaloid nigellicine. From a chemical point of view, one of the more interesting properties of this class of molecules is the possibility of forming an N-heterocyclic carbene by thermal decarboxylation. In this paper we have studied the carbene generation by decarboxylation of 1,2-dimethyl indazolium-3-carboxylate, using vibrational

  3-羧酸吲唑鎓是一个分子，可以发现为几个伪交叉偶联的介观甜菜碱的核，例如生物碱尼古丁碱。从化学角度来看，这类分子更有趣的特性之一是有可能形成N-杂环卡宾通过热脱羧。在本文中，我们使用振动（红外和拉曼光谱）和量子化学计算研究了1,2-二甲基吲哚鎓-3-羧酸酯的脱羧生成卡宾。正态模式分析使我们能够分析脱羧后拉伸力常数的变化并建立光谱结构关系。我们还研究了5卤素（氟，氯）取代对卡宾生成的影响。计算了三种衍生物的脱羧能分布。当从过渡态到最终产物时，获得了能量路径的交叉。
• Anticancer agent
  申请人：Nagano Tetsuo

  公开号：US09156827B2

  公开（公告）日：2015-10-13

  An anticancer agent comprising a compound represented by the formula (I) [R1 represents hydrogen atom, hydroxyl group, a C1-6 alkoxy group and the like; R2 and R3 represents hydrogen atom, a halogen atom, a C1-6 alkyl group and the like; R4 represents hydrogen atom, a C1-6 alkyl group, a C1-6 alkylsulfonyl group and the like; R5 represents hydrogen atom or a substituent; represents a single bond or a double bond; R6 and R7 represents hydrogen atom, a C1-6 alkyl group and the like; R8 represents hydrogen atom, a C1-6 alkyl group and the like; A represents —O—, —S—, or —CH2—; D represents —C═ or —N═; X represents methylene group, —O—, or —CO—; Q represents —N═ or —C(R8)═; and Y represents a heterocyclic group or amino group], which shows a superior inhibitory activity against pim-1 kinase.

  一种抗癌剂，包括由公式（I）所代表的化合物 [ R1 代表氢原子、羟基、C1-6烷氧基等； R2 和 R3 代表氢原子、卤素原子、C1-6烷基等； R4 代表氢原子、C1-6烷基、C1-6烷基磺酰基等； R5 代表氢原子或取代基； 表示单键或双键； R6 和 R7 代表氢原子、C1-6烷基等； R8 代表氢原子、C1-6烷基等； A 代表-O-、-S-或-CH2-； D 代表-C═或-N═； X 代表亚甲基基、-O-或-CO-； Q 代表-N═或-C(R8)═； Y 代表杂环基或氨基]，该化合物对pim-1激酶具有卓越的抑制活性。