4-amidino-2,3-dihydro-1H-inden-1-one hydrochloride | 138764-19-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 4-amidino-2,3-dihydro-1H-inden-1-one hydrochloride
• 英文别名: 4-amidinoindan-1-one hydrochloride；4-amidino-1-indanone hydrochloride；1-Oxo-2,3-dihydro-1H-indene-4-carboximidamide hydrochloride；1-oxo-2,3-dihydroindene-4-carboximidamide;hydrochloride
• CAS: 138764-19-9
• 化学式: C₁₀H₁₀N₂O*ClH
• 分子量: 210.663
• InChiKey: MWFDDDJSDSYEHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.52
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  66.9
• 氢给体数：
  3
• 氢受体数：
  2

安全信息

• 海关编码：
  2925290090

反应信息

• 作为反应物：
  描述：

  氨基胍碳酸氢盐 、 4-amidino-2,3-dihydro-1H-inden-1-one hydrochloride 在 盐酸 作用下， 以 水 为溶剂， 反应 20.0h， 以72%的产率得到2-(4-aminoiminomethyl)-2,3-dihydro-1H-inden-1-ylidene dihydrochloride
  参考文献：
  名称：

  4-Amidinoindan-1-one 2'-amidinohydrazone: a new potent and selective inhibitor of S-adenosylmethionine decarboxylase

  摘要：

  Two isomeric amidino-2-acetylpyridine amidinohydrazones, 11 and 12, and 4-amidinoindanone amidinohydrazone, 17, have been synthesized and tested for inhibition of S-adenosylmethionine decarboxylase (SAMDC) and diamine oxidase and for antiproliferative activity against T24 human bladder carcinoma cells. Compound 11 inhibited SAMDC with an IC50 of 10 nM and was 140- and >500-fold more potent than methylglyoxal bis(guanylhydrazone) (MGBG) and 12, respectively. The difference in potency between 11 and 12 was interpreted with the help of molecular modeling and appeared to be associated with two different low-energy conformations of the compounds. Compound 17 which represents a conformationally constrained analogue of 11, was superior to the latter and MGBG with respect to selective inhibition of SAMDC and antiproliferative activity, and is of interest as a potential anticancer agent and a drug for the treatment of protozoal and Pneumocystis carinii infections.

  DOI：

  10.1021/jm00067a014
• 作为产物：
  描述：

  Ethyl 1-oxo-2,3-dihydro-1H-indene-4-carbimidothioate 在 氯化铵 作用下， 以 乙醇 为溶剂， 反应 20.0h， 生成 4-amidino-2,3-dihydro-1H-inden-1-one hydrochloride
  参考文献：
  名称：

  4-Amidinoindan-1-one 2'-amidinohydrazone: a new potent and selective inhibitor of S-adenosylmethionine decarboxylase

  摘要：

  Two isomeric amidino-2-acetylpyridine amidinohydrazones, 11 and 12, and 4-amidinoindanone amidinohydrazone, 17, have been synthesized and tested for inhibition of S-adenosylmethionine decarboxylase (SAMDC) and diamine oxidase and for antiproliferative activity against T24 human bladder carcinoma cells. Compound 11 inhibited SAMDC with an IC50 of 10 nM and was 140- and >500-fold more potent than methylglyoxal bis(guanylhydrazone) (MGBG) and 12, respectively. The difference in potency between 11 and 12 was interpreted with the help of molecular modeling and appeared to be associated with two different low-energy conformations of the compounds. Compound 17 which represents a conformationally constrained analogue of 11, was superior to the latter and MGBG with respect to selective inhibition of SAMDC and antiproliferative activity, and is of interest as a potential anticancer agent and a drug for the treatment of protozoal and Pneumocystis carinii infections.

  DOI：

  10.1021/jm00067a014

文献信息

• Hydrazones
  申请人：Ciba-Geigy Corporation

  公开号：US05395855A1

  公开（公告）日：1995-03-07

  Compounds of formula I ##STR1## wherein A, X, Z and R.sub.1 -R.sub.5 are as defined in the description, and their salts have valuable pharmaceutical properties and are effective especially against tumors. They are prepared in a manner known per se.

  公式I的化合物##STR1##其中A，X，Z和R.sub.1-R.sub.5如描述中所定义，并且它们的盐具有有价值的药物特性，特别是对抗肿瘤有效。它们的制备方法已知。
• Imidazole derivatives, their preparation and their use as
  申请人：Novartis AG

  公开号：US05840911A1

  公开（公告）日：1998-11-24

  Described are compounds of formula I ##STR1## wherein R.sub.1 is hydrogen or hydroxy; R.sub.2, R.sub.2 ' and R.sub.2 " are each independently of the others hydrogen or a substituent other than hydrogen; either R.sub.3 is hydrogen or a substituent other than hydrogen and R.sub.4 is hydrogen or lower alkyl, or R.sub.3 and R.sub.4 together form a divalent radical of the formula --(CH.sub.2).sub.n -- wherein n is 2 or 3; R.sub.5 and R.sub.6 are each independently of the other hydrogen, alkyl or aryl; and either R.sub.7 and R.sub.8 are each hydrogen, or R.sub.7 and R.sub.8 together form a bond; tautomers thereof, provided that at least one tautomerisable group is present; and salts thereof. The compounds inhibit the enzyme S-adenosylmethionine decarboxylase and are suitable, for example, for the treatment of tumours and protozoal infections.

  本文描述了I式化合物，其中R1为氢或羟基；R2、R2'和R2"各自独立地为氢或非氢取代基；R3为氢或非氢取代基，R4为氢或较低的烷基，或R3和R4共同形成公式-(CH2)n-的二价基团，其中n为2或3；R5和R6各自独立地为氢、烷基或芳基；R7和R8要么各自为氢，要么共同形成键；其互变异构体，只要至少存在一个可互变异构基团；以及其盐。这些化合物抑制了S-腺苷甲硫氨酸脱羧酶酶，并适用于例如治疗肿瘤和原虫感染的治疗。
• IMIDAZOLE DERIVATIVES, THEIR PREPARATION AND THEIR USE AS S-ADENOSYLMETHIONINE DECARBOXYLASE (=SAMDC) INHIBITORS
  申请人：Novartis AG

  公开号：EP0808309B1

  公开（公告）日：2004-10-06
• US5395855A
  申请人：——

  公开号：US5395855A

  公开（公告）日：1995-03-07
• US5461076A
  申请人：——

  公开号：US5461076A

  公开（公告）日：1995-10-24